Connecticut is home to boundless beauty. We all know this — but sometimes we could all use a reminder. If you’re looking for the spectacular scenery that only The Nutmeg State can offer, we have the perfect itinerary. This waterfall and cave road trip in Connecticut leads you to some extraordinary places, and the entire drive only takes about 4.5 hours. Of course, you may want to spread this trip out over two days. These exceptional sights are too breathtaking to breeze by. What are you waiting for? There’s no need to Google ‘waterfalls near me.’ These caves and waterfalls will make you fall in love with Connecticut all over again.

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Because this waterfall and cave road trip creates a loop, you can easily begin your journey from any point you choose. Check out the map for detailed directions.
1. Judges Cave -- New Haven
Judges Cave, New Haven, CT 06515, USA
Debbie Samilenko/AllTrails
Not many people know there is a fascinating cave hiding inside West Rock Ridge State Park. If you're craving a refreshing walk, embark on The Regicides Trail. This seven-mile hiking trail leads to Judge's Cave, an intriguing piece of Connecticut's history.
Debbie Samilenko/AllTrails
Though it may not look like much at first, this place is one of the most fascinating caves in Connecticut. In 1649, 59 British judges sentenced King Charles I to death, which put Oliver Cromwell in power. But 11 years later, Charles II took the throne, and he wanted revenge against the judges who condemned his father. In order to escape the torturous death awaiting them, judges Whalley and Goffe fled to New Haven. Local Puritans helped the men stay safe within this tiny cave shelter. Thankfully, this story has a happy ending. After living within the cave walls for several weeks, the judges made their way to Massachusetts, where they lived the rest of their lives.
2. Kent Falls -- Kent
Kent Falls State Park, 462 Kent Cornwall Rd, Kent, CT 06757, USA
Daniel Hartwig/Flickr
Ben Pollard/Flickr
No nature-focused road trip would be complete without a stop at Kent Falls State Park. This 250-foot waterfall continues to capture our imaginations time after time. If you're a photography enthusiast, this is the ultimate place to snap some shots. For the latest information about hours and regulations, visit the Connecticut DEEP website.

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3. Indian Council Caves -- Barkhamsted
Indian Council Caves, CT-219, Barkhamsted, CT 06063, USA
Amy Dills/AllTrails
Though not as famous as some of our notable state parks, Tunxis State Forest belongs on every Nutmegger's bucket list. Here, you'll not only find peaceful hiking paths and astonishing wildlife -- you'll also come across Indian Council Caves.
Google Images/Marius Bragagiu
To reach this natural wonder, hike the 5-mile Indian Council Caves Trail. This peaceful pathway will lead you under a verdant forest canopy. Soon, you'll see the majestic boulders that have come to be known as Indian Council Caves. Of course, these aren't true secret caves, but they're breathtaking nonetheless.
4. Enders Falls -- Granby
Enders State Forest, Granby, CT 06035, USA
Jcanhottie/TripAdvisor
Ump22/TripAdvisor
Next, pay a visit to Enders State Forest in Granby. You'll want to wear your heavy duty hiking shoes here -- the steep slopes and slippery rocks often prove hazardous. We promise the effort is worth it, though. When you reach the multi-level cascade, you'll feel like you've entered another world. For the latest information regarding hours and closures, visit the Connecticut DEEP website.
5. Chapman Falls -- East Haddam
Chapman Falls, East Haddam, CT 06423, USA
Joe Podbielski/Getty Images
pmstephens/Getty Images
Don't go home without experiencing the grandeur of Chapman Falls. This waterfall staircase in Connecticut looks like something from a dream. Visitors can view this natural attraction from the rocks at the bottom or from the walkway at the top. No matter where you gaze at these 60-ft cascades, you'll be blown away.

 

What do you think of our caves and waterfalls road trip in Connecticut? Are there any other places you’d like to add to your route? Share your thoughts with us in the comments below!

Still wondering about the best waterfalls in Connecticut? We’ve got you covered! For a short-and-sweet day trip, check out these easy-access waterfalls in Connecticut.

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More to Explore

Waterfalls Near Me

Elisa Regulski | March 04, 2022

Does Connecticut have any natural wonders?

The Nutmeg state is home to some astonishing natural wonders, but nothing quite compares to Kent Falls State Park. This picturesque destination is home to one of the best waterfall hikes in Connecticut. In fact, it was named one of the most beautiful places in the state! When you gaze up at its rushing waters, you’ll feel like you’ve stepped inside another world. Of course, this is just the beginning of what our wonderful state has to offer. For more travel ideas, take a look at our list of the best natural wonders in Connecticut.

Which state parks should I visit in Connecticut?

We love visiting Chatfield Hollow State Park in Killingworth, Connecticut. You’ll find astonishing views whenever you visit, but it’s especially magical during autumn. When the leaves turn hues of red, yellow, and orange, you’ll be blown away by the views. If you’re craving a beach day, visit Hammonasset Beach State Park in Madison. These peaceful sights will leave you feeling refreshed and renewed. For more ideas, check out our list of the best state parks in Connecticut.

What are the best waterfall hikes in Connecticut?

If you’re looking for the best waterfall hikes in Connecticut, you’re in luck! There are so many wonderful places to explore in this state. For starters, hike to Indian Well Falls in Shelton. Yes, the hike will only take about five minutes, but trust us, it’s worth driving out to. The 15-foot waterfall is nothing short of spectacular. And because it’s so short and sweet, it’s one of the best kid-friendly hikes in Connecticut. Need more ideas? We’ve rounded up a list of the best easy waterfall hikes in Connecticut. You can’t go wrong with any of these!

Related Articles

Featured Addresses
Judges Cave, New Haven, CT 06515, USA
Kent Falls State Park, 462 Kent Cornwall Rd, Kent, CT 06757, USA
Indian Council Caves, CT-219, Barkhamsted, CT 06063, USA
Enders State Forest, Granby, CT 06035, USA
Chapman Falls, East Haddam, CT 06423, USA